Thionyl Chloride → 6-(5-Fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chloride

HRID 1290919Notes

Reaction equation

HRID 1290919 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([CH:19]=1)[C:7]([NH:9][C:10]1[N:15]=[CH:14][C:13]([C:16](O)=[O:17])=[CH:12][CH:11]=1)=[O:8].S(Cl)([Cl:23])=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([CH:19]=1)[C:7]([NH:9][C:10]1[N:15]=[CH:14][C:13]([C:16]([Cl:23])=[O:17])=[CH:12][CH:11]=1)=[O:8]

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 18387469HCID 18387469, compound

Product 1

HCID 155082506-(5-Fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chloride

Procedure

A mixture of 6.2 g of 6-[(5-fluoro-2-methylbenzoyl)amino]pyridine-3-carboxylic acid and 23 ml of thionyl chloride is refluxed for 1 hour. An additional 12 ml of thionyl chloride is added and the mixture refluxed for 0.5 hour. The mixture is concentrated to dryness under vacuum and 30 ml of toluene added to the residue. The toluene is removed under vacuum and the process (add toluene and remove) is repeated to give 7.7 g of crude product as a solid.

Workup

  1. temperatureis refluxed for 1 hour
  2. temperaturethe mixture refluxed for 0.5 hour
  3. concentrationThe mixture is concentrated to dryness under vacuum and 30 ml of toluene
  4. additionadded to the residue
  5. customThe toluene is removed under vacuum
  6. additionthe process (add toluene and remove)

Sources & evidence

ORD record
ord-0a81d9184ecc44f2bfd003caa4728901
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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